Okay, seriously? How in all that is holy are you supposed to get started in this game? Even after selling my ships' product of Leather and Cacao at the beginning of the game, I still do not have nearly enough cash to restock an entire crew - something which I have not even been able to accomplish yet because of how ridiculously absurd this mod is becoming. Even with what - 20 out of the max amount of sailors applied to the starting Sloop I still find myself struggling with managing my upkeep costs. Now before you say, 'Just sail with less crew at the start' that brings me to my next point.

Literally the second I leave the starting island I get convoys of chasing ships coming after me. It's absurd that a ship will literally chase me from Nevis all the way to Tortuga (no, that's not a hyperbole, that genuinely did happen to me) and even more absurd than that? I can be well within the range of a Fortification on any of the friendly islands and yet they still want to fight. Like - what? How is that supposed to make any sort of sense? Keep in mind i'm not talking about massive SOTL's here, I'm talking about schooners, brigantines, even bloody war tartanes that value my ship over everyone else's - if it means getting obliterated by a Fort, it seems the AI think it's worth it as long as I'm sunk.

Speaking of War Tartanes - boarding such a tiny, insignificant ship should be an easy task. Lmao, not really, because somehow the AI still has more crew members than I do. For such a small ship in comparison to a Sloop I mean...come on. Really?

Now that I have that off of my chest, I would like to ask if anyone else has faced these problems and has any solutions? Many thanks.

The lack of starting money is just one of the little things I didn't care for about the mod. I added a line to the console to give myself just enough starting money to get everything equipped, but not enough to buy anything useful. I don't consider that a cheat unless I'm playing on a higher difficulty level. Also, unless you intend to get into a lot of boarding action, you don't need a lot of crew. In fact, your ship will probably sail a bit faster if you don't have a full crew, and it will require less food and your monthly payments to the crew will be less.

If someone wants to chase you that far, lure then in range of a fort that is hostile to them and let the fort do all the work. Feel free to board them at some point, or just pick up whatever cargo the sunken ship drops.

If you expect to board another ship, reduce its crew with grapeshot first. It may take a lot of shots.

Ships chasing you all the way to a fort that sinks them has been a feature of the Storm engine games from the beginning.

Also, unless you intend to get into a lot of boarding action, you don't need a lot of crew. In fact, your ship will probably sail a bit faster if you don't have a full crew, and it will require less food and your monthly payments to the crew will be less.

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Yes but like I said, it's really a lose-lose scenario for me: If I don't have enough crew members = I get shredded when a Pirate or enemy attacks. If I max my capacity to avert this = I bleed money.

If someone wants to chase you that far, lure then in range of a fort that is hostile to them and let the fort do all the work. Feel free to board them at some point, or just pick up whatever cargo the sunken ship drops.

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The last time I did this, the Fort guns did absolutely nothing. By that I mean, I sailed into their protective range and let them do the firing, only to see more cannons splash into the water then actually hit. And I cannot do anything about it but just sit there and soak up more damage, damage that I cannot afford. And to add to this frustration, the second I spacebar out into the map I get chased down, in port by a fresh new enemy.

Here's another thing that passed my mind also. The only time when I've seen my character level up and actually successfully board many different ships is when I played the Pirate faction = supposedly not recommended for new players. Do you see what I mean by this?

All in all it totally chips away my patience with this game. I was this close to uninstalling it last night but I figured why let something so insignificant beat me?

I can't give you advice on specifics. Perhaps one of the modders or someone who is an expert playing the mod can help.

You have a few options. Play the pirate faction if you've found you can be successful. Play the stock game without any mods. Try another mod. Try another game: PotC with the New Horizons mod is quite good, and Sea Dogs: To Each His Own on Steam is quite good as well.

I've got the most experience in the last one, TEHO. In that game the only time you'll have ships chasing you like that are if you get a bounty on your head from one of the countries you've attacked. Some people complain about not being able to leave port when they've attracted too many bounties. While you can get chased by pirates occasionally, there are ways to avoid it.

Stock games are usually fairly well balanced. With mods, you never know. New Horizons is balanced. TEHO was intended to be difficult as a design decision, and this is built into the story line quests, but I've never seen the situation you've described above in TEHO, although it could happen if you attack a lot of some nation's ships.

What really helped for me in the beginning was grinding. Well, half of the game I was basically grinding. For cash and experience.

Starts are really slow, especially if you don't pick Peter Blood for quality intro that gives you great start experience, cash, officers and even one of the best ships.

But even without that, the beginnings are very tough. But doable. You should avoid most of the sea contact unless it's quest related (stolen ship, governor's pirates) or a ship just sightly better than yours, because otherwise, without good gunner, carpenter and doctor, the AI will just decimate you quickly.
Then come the other quests grind. Go to town, visit governor for quest, visit moneylender for jewelquest, visit tavern for passenger, visit port controller for logbook quest, do all quests, repeat. Get cheap officers early, get the skill of experience share quickly and grind. Set fellas as fighters and fight bandits and skeletons.
Get a corvete and a frigate type ship quick for speed, do treasure quests. For training, keep doing port controller's quests for good XP, governor's for loyalty (assuming you want to do the national quest first) and pirate propositions to fight the shipwrecked troops (a little bit of savescumming before talking to the captains before quest) for good amounts of valuable cargo.

About that, trading comes in later with good treasurer but if you're doing passenger or escort quest, check the tradebook and buy/sell as supply and demand goes (visit towns often, prices change, and don't only follow the green/blue arrows but mainly prices). At first, you'll be looking at very few % profits, later you will be selling for triple the value.
Do the austin quest as soon as possible (read the walkthrough if you don't mind going this way) and some other main quests, I recommend to train in light or medium weapons.

Sometimes I found myself circling around the map just doing low level trading, treasure hunting and repeatable quests while waiting for a better ship, officers and items to begin with higher quest. All while avoiding most pirates or attackers. No shame in that. It gets better at around level 20, then it goes well.

Now, I play GOF 2.6 and I usually play as Diego so the starting ship I get is quite powerful. I'm not sure how useful this advice will be for you in your situation (and I understand this is an older post but perhaps people will find value in this).

For me, I've found that doing chartered cargo runs for merchants is the best way to get money early game. For my starting ship I can usually make 20k a run and so I do that a few times until I have a fully equipped ship and crew, along with some officers. After that I go pirate hunting and start boarding and capturing ships and selling them at a shipyard.

Hopefully that will give you some advice on how to proceed going forward.